Oakland Vacations from $396
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Americas Best Value Inn Pittsburgh Airport
Price was $516, price is now $396 per person
$396
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
6.6/10 (1,002 reviews)
It is great place to stau, room was clean, bigger and staff is friendly. I reached at 1am so didnt get free shuttle but they gave me number of global parking shuttle and they charge $10 but you have option. I would recommend this place
Reviewed on Mar 19, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was $898, price is now $681 per person
$681
per person
Jun 16 - Jun 19
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
It’s a nice hotel with friendly staff. I think you should give a discount or free parking for people staying at the hotel. The cost to parks adds up quick.
Reviewed on Apr 10, 2026
Pittsburgh Marriott City Center
Downtown Pittsburgh
Price was $736, price is now $572 per person
$572
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.2/10 Very Good! (1,186 reviews)
The hotel is clean and spacious. Could do with a refresh (power points or charge ports near the bed).
But what is outstanding is their staff. 100% every interaction was awesome. Polite. Professional. Warm and welcoming. Is something was needed, they did it. If something was uncertain, they cleared it up. They handled mail and packages. Remembered important details and got things resolved. Always with a polite smile and no extra charges.
THIS is how hospitality should work. Orlando, Vegas and the big resorts can learn plenty from the Marriott Pittsburgh!!
Reviewed on Apr 13, 2026
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Downtown Pittsburgh
Price was $643, price is now $501 per person
$501
per person
Jun 16 - Jun 19
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.2/10 Very Good! (1,059 reviews)
The front desk staff were excellent
Reviewed on Apr 9, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,278 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
$155 nightly
The price is $177 total per night from Apr 27 to Apr 28
$177 total
Apr 27 - Apr 28
Total with taxes and fees
9/10 Wonderful! (673 reviews)
Nice room. Good bar and breakfast area.
Reviewed on Apr 8, 2026
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
$144 nightly
The price is $164 total per night from May 11 to May 12
$164 total
May 11 - May 12
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
Never a good sign when your room comes with earplugs for “Neighborhood Sounds”. Beware: all rooms with two beds are facing and adjacent to a very busy turnpike. We didn’t get a good rest and will never stay there again.
Reviewed on Apr 13, 2026
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$260 nightly
The price is $296 total per night from Apr 26 to Apr 27
$296 total
Apr 26 - Apr 27
Total with taxes and fees
9.2/10 Wonderful! (762 reviews)
Outstanding. But room was way too bright with all kinds of lights in the room.
Reviewed on Apr 12, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Carnegie Museum of Natural History
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Pittsburgh: Museum of Illusions Entrance Ticket
$29
per adult
80% of travellers recommend
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
$84
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
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- University of Pittsburgh
- University of Pittsburgh Medical Center
- The Nationality Rooms
- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
- Phipps Conservatory
- Schenley Park
- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
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- Market Square
- Visit Pittsburgh
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- Ppg Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.